2,5-dibromo-3,4-dihexylthiophene-1,1-dioxide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 2,5-dibromo-3,4-dihexylthiophene-1,1-dioxide
• 英文别名: 2,5-Dibromo-3,4-dihexylthiophene 1,1-dioxide
• 化学式: C₁₆H₂₆Br₂O₂S
• 分子量: 442.255
• InChiKey: SIXKUDGAHFBTRU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  42.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,5-dibromo-3,4-dihexylthiophene-1,1-dioxide 在 正丁基锂 、 三丁基氯化锡 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 19.0h， 生成 5-dimethyl(chloromethyl)silyl-3'',4''-dihexyl-2,2':5',2'':5'',2''':5''',2''''-quinquethiophene-1'',1''-dioxide
  参考文献：
  名称：

  Oligothiophene Isothiocyanates as a New Class of Fluorescent Markers for Biopolymers

  摘要：

  The regioselective synthesis of fluorescent oligothiophene isothiocyanates is described. The isothiocyanates were reacted with bovine serum albumin (BSA) following standard procedures and the optical properties of the oligothiophene-BSA conjugates were analyzed as a function of oligomer concentration, time, and irradiation power. The oligothiophene-BSA conjugates were chemically very stable and their photoluminescence characteristics persisted unaltered for several months. Photoluminescence data relative to the conjugate of an oligothiophene-S,S-dioxide isothiocyanate with monoclonal anti-CD8 antibody are reported. No fluorescence quenching was observed following the binding of the isothiocyanate to the antibody and the conjugate displayed high chemical stability and photostability.

  DOI：

  10.1021/ja011209v

文献信息

• 3,4-Ethylenedioxy-substituted bithiophene-alt-thiophene-S,S-dioxide regular copolymers. Synthesis and conductive, magnetic and luminescence properties.
  作者：Anna Berlin、Gianni Zotti、Sandro Zecchin、Gilberto Schiavon、Massimo Cocchi、Dalia Virgili、Cristiana Sabatini

  DOI：10.1039/b206669f

  日期：2003.12.10

  Polyconjugated regular bithiophene-alt-thiophene-S,S-dioxide copolymers were produced by anodic coupling of variously 3,4-ethylenedioxy-substituted 2,5-bis(2-thienyl)thiophene-S,S-dioxide. The polymers were characterized by cyclic voltammetry, FTIR reflection-absorption and UV-vis spectroscopy, MALDI-TOF mass spectroscopy, electrochemical quartz crystal microbalance, in situ ESR and in situ conductivity techniques, photo- and electro-luminescence measurements. The regular alternation of electron-rich and -poor thiophene rings in the polymer chain operated by the ethylenedioxy and S,S-dioxide moieties produces a finite window of conductivity. Alkyl-protection of the β-positions of the thiophene-S,S-dioxide ring gave low-defect and soluble oligomers which were investigated in single-layer organic light-emitting devices (OLEDs). Photoluminescence quantum efficiency of ca. 1% and external electroluminescence quantum efficiencies of 0.01% photon/electron at a luminance of 100 cd m−2 were obtained.

  通过阳极偶联不同的3,4-乙二氧基取代的2,5-双(2-噻吩基)噻吩-S,S-二氧化物制备了聚共轭常规联噻吩-替代噻吩-S,S-二氧化物共聚物。通过循环伏安法、FTIR反射吸收和紫外可见光谱、MALDI-TOF质谱、电化学石英晶体微天平、原位ESR和原位电导率技术、光致发光和电致发光测量对聚合物进行了表征。聚合物链中由亚乙基二氧基和S,S-二氧化物部分控制的富电子和贫电子噻吩环的规则交替产生了有限的电导率窗口。噻吩-S,S-二氧化物环的β-位置的烷基保护产生低缺陷且可溶的低聚物，并在单层有机发光器件（OLED）中进行了研究。光致发光量子效率约为在亮度为 100 cd m−2 时获得了 1% 和 0.01% 光子/电子的外部电致发光量子效率。
• 3,4-alkylenedioxythiophenedioxide compounds and polymers comprising monomeric units thereof
  申请人：AGFA-GEVAERT

  公开号：US20040097741A1

  公开（公告）日：2004-05-20

  A 3,4-alkylenedioxythiophenedioxide compound represented by formula 1 in which: A represents a C 1-5 -alkylene bridge; R represents an optionally substituted C 1-24 -alkyl, C 3-18 -cycloalkyl, C 1-18 -alkoxy or polyethylene oxide group (optionally with at least one substituent selected from the group consisting of an alcohol, amide, ether, ester or sulphonate group) or an optionally substituted aryl group; a polymer comprising monomeric units represented by formula (I); an aqueous dispersion of a polymer comprising monomeric units corresponding to at least one compound according to formula (I) and a polyanion; a chemical polymerization process for preparing the aqueous dispersion comprising the steps of: (i) providing a solution of a polyanion; (ii) adding a compound according to formula (I) and a thiophene or pyrrole compound to the solution provided in step (i); and (iii) adding an oxidizing or reducing system to the mixture provided in step (ii); a printable paste containing the aqueous dispersion; an electroconductive layer containing the polymer; the use of the electroconductive layer in a light emitting diode; an antistatic layer containing the polymer; and an electroconductive pattern and a process for preparing the electroconductive pattern.

  一种 3,4-烷基二氧噻吩二氧化物化合物，由式 1 代表 1 其中A 代表 C 1-5 -烯桥；R 代表任选取代的 C 1-24 -烷基、C 3-18 -环烷基、C 1-18 -烷氧基或聚环氧乙烷基团(可任选具有至少一个选自醇、酰胺、醚、酯或磺酸盐基团组成的组的取代基)或可任选取代的芳基；由式(I)代表的单体单元组成的聚合物；由与至少一种根据式(I)的化合物相对应的单体单元和聚阴离子组成的聚合物的水分散液；制备该水分散液的化学聚合工艺，包括以下步骤：(i) 提供聚阴离子溶液；(ii) 向步骤(i)中提供的溶液中加入根据式(I)的化合物和噻吩或吡咯化合物；(iii) 向步骤(ii)中提供的混合物中加入氧化或还原体系；含有水性分散体的可印刷浆料；含有聚合物的导电层；导电层在发光二极管中的用途；含有聚合物的抗静电层；以及导电图案和制备导电图案的工艺。
• Conformational profile, energy barriers and optical properties of quinquethiophene-S,S-dioxides
  作者：Alessandro Bongini、Giovanna Barbarella、Laura Favaretto、Giovanna Sotgiu、Massimo Zambianchi、Daniele Casarini

  DOI：10.1016/s0040-4020(02)01398-4

  日期：2002.12

  Theoretical calculations, dynamic NMR experiments and absorption and photoluminescence data in solution are reported for a series of quinquethiophene S,S-dioxides substituted with alkyl groups of variable size and steric hindrance. Ab initio B3LYP/6-31G* and force field MM3 theoretical calculations show that the energy barriers for rotation around the inter-ring C-C bonds amount to a few kcal/mol even in the presence of very bulky substituents such as the cyclohexyl group. Dynamic NMR data were in agreement with the results of theoretical calculations. It was found that changing the steric hindrance of the substituents leaves the emission and photoluminesce properties unaltered. However, the photoluminesce intensities and wavelengths of all compounds were found to be very sensitive to solvent variations. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Functionalized thiophene oligomers and their use as fluorescent markers
  申请人：CONSIGLIO NAZIONALE DELLE RICERCHE

  公开号：EP1160246B1

  公开（公告）日：2007-05-09
• US6841669B2
  申请人：——

  公开号：US6841669B2

  公开（公告）日：2005-01-11